Business of Pleasure
by General-Fullbuster
Summary: Jack Overland is asked by his boss to take his daughters, Anna and Elsa, into his office as secretaries. With the deal that if Elsa can last a year under him, she will be given her own office to run. With specific instructions not to take it easy on either girl, he intends to show them just how tough the business world can be. Spankfic. Contains spanking. Don't like, don't read.
1. Chapter 1

**A/N: Alright, few things to address for all of the people who follow my work. No, I haven't given up on Master Arc. I'm still planning on updating it. Those chapter's tend to take long because of both my schedule and that fact that it's a bit more detailed than most of my other works. I still plan to continue my other works as well, whenever I get the spark for them. (Whole reason I started those was because they're something I do when I'm in the mood to)**

**Now, with that said, hope you enjoy this story. This is more of a introduction chapter than anything (I guess that's the first chapter of any story though...) and some of the characters are a little OOC. But like I say for a number of my stories, just go with it. I'm not here to craft some Shakespearean quality work, I'm here to write about some spanked bottoms. You're going to have to humor me to get there. **

**Enjoy!**

* * *

Jack Overland never thought he'd grow up to be the head of some office. He had always figured he'd end up working in a grocery store or delivering packages or something. Never in his wildest dream did he imagine he'd be making six figures for, what was honestly, very little work. But it seemed like charisma and charm could carry a person pretty far in the world.

It had been a stroke of luck that he'd ran into Mr. Arendelle, head of Arendelle INC and one of the biggest billionaires on the planet. Of course he'd had no idea who he'd been at the time. He just thought he was some regular guy and treated him as such. He'd made of a hell of a first impression on him, because he's offered him a job in his company. It had been a low level position, though much higher paying then the job Jack had at the time, which he excelled at.

Jack had known very little about business when he started, but a charming smile and a silver tongue were really all you needed once you had the basics. Of course he'd picked up on the ins and outs of everything as he progressed, and before he knew it he was running his own office. He was a true example of rags to riches.

Being in his position carried a lot of perks. The first being how little he actually had to work. It was kind of ironic. The higher up you got, the less you had to actually do. He passed on a lot of his stuff to his employees, making sure to check over what they'd handed in to make sure it was all correct.

Another of the perks was the number of sexy secretaries around the office, along with the office discipline they answered to. Mr. Overland held very traditional values, and it reflected in his the way he ran his company. To him, the best cure for a lady who was misbehaving or making mistakes was a well smacked bottom. So all their secretaries were meant to sign a document acknowledging that they could and would submit to such if they agreed to take the job. With that kind of stipulation you wouldn't think they'd have so many people applying. But there were a lot of attractive women looking for well paying and relatively simple jobs, even if it came at the cost of a sore backside.

It also served as a way to keep the men who ran the office happy and loyal. Not many guys were ready to give up the perks that came with their positions, even if a rival company was willing to shell out more money. Jack certainly wouldn't have. He had taken full advantage of their 'correctional system' since he was assigned his first secretary.

There was no better way to kill boredom or unwind from a tough day than to have a nice well rounded bottoms across your lap to spank. And with well over a dozen secretaries working in his office, there was hardly a day that went by where he didn't get to discipline at least one of them.

Like now.

Rapunzel Corona was a sweet girl. Nice figure, long blonde hair, and a nice pert little bottom. Her pink blouse didn't show off much cleavage, but her bust was still very apparent, and her purple pencil skirt hugged her bottom tightly and showed off every curve. She was currently bent over his desk, rear up in the air and trembling as she awaited the next stinging swat of his leather paddle.

SMACK!

"OH!"

Jack watched amused as her bottom danced, her purple high heels clicking against the floor as she jumped from side to side. She had always been such a jumpy little thing. "Settle down now Punzie. I haven't even lifted your skirt up yet," he said chuckling. She was probably getting a bit pink in the cheeks by now, so he'd peel that short little skirt of hers up soon.

"Oh, please no sir! Not that!" she whined.

Jack nodded. "Oh yes, that. I think you've earned a nice bare bottom punishment today," he said getting ready to swing again. She let out a groan as she braced herself for the next swats, but before he could follow through with it a voice came over his intercom.

"Mr. Overland sir?"

Jack sighed and put the paddle down before walking around his desk. Rapunzel sighed, looking more than a bit relieved to have a break. "Honey, I'm in the middle of a disciplinary correction right now. You know I don't like being interrupted during that time. Unless you would like to join us maybe?" he asked.

"No sir! I'm sorry. It's just, you have a visitor, and I thought it was urgent to let you know."

Jack raised an eyebrow. He didn't have meetings scheduled for today. Not unless another of his secretaries slipped up. If that was the case someone would be going up with a striped bottom today. "May I ask who this visitor is?"

"It's Mr. Arendelle sir."

Jack looked a bit surprised. Not because he was worried or anything. He was on very friendly terms with his boss, and he stopped by just to check up on him and chat regularly. It was just that he usually called ahead first before doing so. A surprise visit like this was rare. "Send him in."

"Right away sir."

Jack looked down towards Rapunzel. "You can stand up," he said. The blonde did so, her face a mix of both confusion and slight hope. "We'll be starting this over again later this evening. For now, go fetch some coffee for Mr. Arendelle and I. And be quick about it."

She nodded. "Yes sir," she said before turning around and quickly making her way out.

As she made her way out of his rather large office, another figure made his way in. Mr. Arendelle. This time however, he was followed by two others. They were young women, both very attractive looking. One was a platinum blonde with her hair tied into a tight braided bun, while the other was a strawberry blonde with her hair braided into two pigtails. His assistants maybe?

"Jack, how have you been my boy!" Mr. Arendelle said holding his hand out.

Jack took it and shook. "Doing fine sir. And you?"

"Oh, I'm alright. Sorry to pop in on your like this. Bit of a hectic morning you see. Hope I wasn't interrupting anything."

"Nothing that can't be taken care of later. It's no problem at all sir," Jack assured. "Always happy to see you."

The older man stood aside and held his hand out to the two women. "And allow me to introduce my daughters. This is Elsa and Anna," he said gesturing towards the platinum and strawberry blonde respectively. Jack hummed. His daughters? He had remembered him mentioning them before, but this was the first time he'd laid eyes on them. They were really something. The one with the pigtails smiled towards him and offered a small wave, while the other just kept a stoic expression. "Girls, this is Jackson Overland. One of my best and brightest managers."

"Hello, nice to meet you," Anna said cheerily.

"It's a pleasure," Elsa said nodding.

Jack smiled and nodded back. "The pleasures all mine," he said before turning back to Mr. Arendelle. "I'm guessing they get their looks from their mother?"

The man burst out in laughter. "Ha! Yes, and thank god for it," he said before gesturing towards his desk. "May I have a seat?"

"Of course sir." The fact that he even bothered asking was something. For being a bit-shot billionaire he was fairly humble.

The man turned towards his daughter. "Girls, could you wait outside for a bit. I need to discuss something with Jack here." The younger of the two smiled and nodded, while the elder let out a small sigh, clearly displeased with being excluded from whatever was going to be discussed. The two turned around and made their way out. As they did, Rapunzel made her way back in carrying two cups of coffee.

"Here you are sir," she said nervously as she set the tray down on the desk.

"Good work Punzie," Jack said before giving the girl a swat on the rear, earning a squeal. She quickly made her way out, not wanting to push her luck.

Mr. Arendelle chuckled as he watched the girl leave. "Still keeping them in line, eh Jack?"

"I learned from the best," Jack said shrugging.

He hummed. "You sure do know how to pick them too. That's quite a lovely one. I wouldn't be able to focus on anything with girls like her running around. But I supposed that's why your one of my best!" he said before leaning forward. "About why I'm here Jack. I need a favor from you."

Ah, so it wasn't business related then? "What could I do for you?"

"It's about my daughters," he started. Now Jack was curious. He didn't have any kids of his own, thank god, so he wasn't sure what the man could need his help for concerning kids. "You see, I want them to start working here. As secretaries."

Jack raised an eyebrow. "Really?" It wasn't really often you heard of a rich kid actually wanting to get their hands dirty, let alone two.

Mr. Arendelle nodded. "Yes, I know. Odd right? But they insisted on getting some real work experience and... well, this is a bit of a test for Elsa you see." Jack sat back, looking intrigued. "Anna is just looking for 'real life' experience. So this is nothing more than indulging her. But Elsa... she's insistent I let her take a part in running the company. She's a smart girl, there's not doubt about that. But you know how I feel about women in the workplace."

Jack nodded. Mr. Arendelle's view of the business world was... well, sexist. There really wasn't any other way to put it. The highest position a women was bound to get if he had any say was an assistant manager, and even then they were little more than glorified secretaries for the actual manager.

"If it were up to me, I'd rather they just occupy their time doing something else. Maybe find a nice young man to settle down with. But those two could never sit still. Elsa has blown through all of her business classes and demand that she be given a chance to prove she can handle herself. So I made a deal with her. If she could take a year here, then I'd get her a higher position in her own office."

Jack nodded in understanding. "So you just need me to give her a position here? Sounds easy."

Mr. Arendelle grunted. "I don't just want you to give her a position. I want you to put her through the ringer. Show just how difficult it is to thrive in the business world."

Jack wanted to make sure he had this right. Because if he was telling her to act as a mentor... well, he supposed he could. He might have had it easy now, but there were plenty of times when the climb up got really tough. Getting a glimpse of it just might scare the girl away. But he had the feeling he meant something else. "Just to clarify sir, are you saying you want me to treat her..."

"Like a secretary," Mr. Arendelle said bluntly. "No special treatment. Don't let her worm her way out of trouble just because she's the bosses daughter."

Jack hummed. "Okay... does she know how things usually go around here?"

"She's aware of the policies, though I doubt she knows how often they're put into use."

"And what about Anna?" he asked.

Mr. Arendelle sighed. "Her too. She's a sweet girl, and all she wants is to spread her wings a bit, but she'd also a bit on the naive side and gets herself into more than a little trouble. I never was good when it came to disciplining those girls. Specially Anna."

Jack scoffed. "You, not good at discipline? Most of the girl's who used to work under you would disagree sir."

"Well, it's different when it's your baby girls. You tend to soften up whenever it comes time to deal out what's due. Not to mention I'm getting on in years, so the time for me to take them to task is long gone," he said before gesturing towards him. "You on the other hand are more than capable of applying a loving and firm hand to them."

He rubbed the back of his head. "I don't know sir. I'm pretty strict with the girls around here. Are you really okay with leaving them here?"

"I am. If Elsa can really hold out working under you, I'll know she wants this badly enough. As for Anna, the girl has needed her bottoms smacked for some time now. And I know you're the man to get the job done. So what do you say my boy?" he asked.

He thought for a moment. Having the two lovely sisters working under him was certainly a delightful thought. And if their father really didn't care about him cracking down on them, then who was he to refuse. "Alright sir, when can they start?" he asked.

Elsa frowned as she waited outside of the office along with her sister. Honestly, why should she have to sit out of a discussion involving _her_ employment. It was ridiculous. Almost as ridiculous as the way her father got on with that smug excuse for a man Jack in there. She had known that he had always been her father's golden boy. He would talk on and on about him with his business buddies. He seemed to think of him like the son he never had, which was again, ridiculous.

The man had always wanted a son. He never said it out loud of course, but it was obvious. He'd wanted a little boy to pass down all his manly knowledge too, and ended up with two girls instead. And in all his old fashion ways he couldn't possibly expect to pass those same skills down to them. The closest he ever got was when Anna took an interest in baseball in middle school, but even then it clear he was humoring her. Not that Anna had noticed at all. She was a very sweet, but very naive little thing.

Elsa hadn't really let it bother her though. Her dad could be absurd, even downright chauvinistic sometimes, but he'd always supported their endeavors and was overall a good father. But when she had said she wanted to start preparing to takeover the company, and he burst out in laughter... well, that had lit a fire in her.

It took some arguing and a lot of valid points made from her, but she had arranged this little deal with him. Make it a year here as Jack's secretary, and she would be given her own office to run. From there it'd just be a matter of climbing up the ladder until he had no choice but to acknowledge her and pass down what was rightfully hers. Not that she should have had to jumped through all these hoops to do it. But if that's what it took, so be it. 

"You think she got spanked?"

Elsa hummed and turned her attention towards her sister. The girl was fidgeting in her seat, and had been ever since they'd seen that blonde come scurrying out of the office earlier. They'd seen her rubbing her tightly skirted butt as she walked around the corner. "Probably," Elsa said bluntly.

She knew all about her father's policy for their female employees. It was downright silly making grown women submit to something like that, and something she planned on putting an end to when she got the reigns.

Anna hummed. "So they really do it. I know I heard daddy mention it sometimes, but... I mean wow. Do you think they mess up enough for it to happen that much?" she asked. She knew she could be a bit of a klutz herself, and while she wasn't sure if her butt was going to be on the line she didn't want to tempt fate.

"I'm sure you don't have to do much to end up over someone's lap around here." She was sure Jack and her father enjoyed dealing out discipline to their staff. Her father always had a pep in his step whenever he'd gotten the chance to punish someone. So did pretty much all of the staff. She didn't think Jack would be any different.

"You don't think daddy will let them spank _us_, do you?" Anna asked.

Elsa scoffed. "Anna, is that what you're worried about? Please. Daddy has never laid a hand on us. Do you honestly think he'll let someone else to it? Besides, he's not going to risk his job just to get a chance at the boss' daughters."

Anna looked somewhat relived at her sister's reasoning. "Huh, guess that's good to know," she said smiling.

The door opened and both her father and Jack stepped out. "Well girls, everything has been sorted out. You start tomorrow, bright and early," her father said smiling towards them.

"I'll be happy to have you. I'm sure you'll be a great help around the office," Jack said.

Anna smiled back at him. "Thank you Jack!"

Elsa simply nodded. "Thank you for the opportunity Mr. Overland. We both look forward to working here."


	2. Chapter 2

**A/N: So for anyone who's curious, this story will eventually dip into M rated territory, and I'll change the rating when it does. I'm only keeping it at T for now because... well, more people see it. Anyway, there you go. Hope you enjoy.**

* * *

"Do you think this makes my butt look big?"

Elsa glanced over towards her sister who was holding her butt up towards the window in their limo. She was using the reflection to try and get a better view of her caboose, which was cover by a rather tight dark green pencil skirt. She was also wearing a light green blouse, and a pair green high heels.

"Yes, but I don't think that can be helped in these things..."

Elsa was also wearing a pencil skirt. Hers was a dark blue. She also had a light blue blouse on and blue high heels. This was apparently the mandatory for all secretaries. Including the heels, which just seemed downright cruel. How were they supposed to get any real work in these things? Her feet would be killing her by the end of today.

Anna pouted. "Do you think I look too childish with the pigtails? Maybe I should wrap it into a bun?" she asked.

Elsa sighed. "Anna, stop focusing on how you look and focus on work."

Her sister huffed. "I am focusing. Looking presentable is an important part of work. I don't want to come into the office looking like a total slob," she argued.

"You look fine. As fine as possible in these anyway," she said looking irritated. She wasn't used to her clothes being so tight on her. She felt like she was walking eye candy for every male in the office. Not that they hadn't been leering at her yesterday. But now it would be even worst.

Anna sat back and smiled. "I don't know. I feel kind of... sexy," she said blushing slightly.

"That's the problem," she muttered. Being sexy shouldn't have been the priority here. It should have been work. One she was in charge, she would have to make some major changes around this place.

The limo came to a stop, and the driver spoke through the speak. "We've arrived Ms. Elsa, Ms. Anna. I hope you have a pleasant day at work. I'll be waiting to pick you up later."

"Thank you," Elsa as she pulled a hundred dollar bill from her pocket. She left it on the seat for him. With how busy they kept all their employees at home Elsa never thought twice about leaving tips behind for them.

The two made their way out of the vehicle and into the building. There was no one there to greet them, not that they needed any direction. They easily remembered where his office was, and made their way up to it.

Elsa spotted a tall blonde girl with glasses. She remembered her from yesterday. She had called Jack over the intercom. "Hello there, we're here to see Jack," Anna said smiling. "We're starting work today."

The girl quickly stood up, recognizing them immediately. "Oh, of course. Ms. Elsa, Ms. Anna," she said nodding.

Anna shook her head. "Oh, you don't have to be so formal. We're not the bosses daughters right now, we're just regular employees. Treat us like any of your other co-workers," she assured.

The girl seemed to loosen up just a bit. "Well, that's nice to hear. It's nice to formally meet you. My name is Aiko by the way. But most people just call me Honey Lemon, or just Honey," she said shrugging.

Anna smiled back at her. "Well Honey, my name is Anna. This is my siser Elsa. It's nice to meet you."

"A pleasure," Elsa said.

"The pleasure's all mine. Now let's get you in. I wouldn't want you running late chatting it up with me. That'd be a first day to remember," she said shuttering. Elsa raised an eyebrow, and Anna looked a bit concerned. "Oh, but I'm sure you two have nothing to worry about. I doubt the same rules will apply."

She pressed the button on the intercom. "Sir, the Arendelle sisters are here."

"_Good, you can send them in._ _Then send for Gogo and tell her to wait outside my office._"

"Yes sir." Honey got up and began leading the two down towards his office. "Good luck you two. Looking forward to working with you. I'll try to fill you in on how everything works later at lunch or something."

Elsa offered her a small smile. "That would be much appreciated."

With that she turned around to go get her co-worker, and Anna and Elsa made their way through the doors into his office. Jack sat at his desk and greeted the two with a smile. "Hello there Anna, Elsa. You both look lovely this morning," he said looking them up and down.

Anna blushed slightly, but looked more flattered then anything, while Elsa narrowed her eyes. "Thanks Jack," Anna said twisting a strand of hair around her finger. Elsa fought back a sigh. Her sister had never been able to think clearly whenever a guy with a handsome face was around.

"Your welcome. And sorry to bring this up, but I think it's best if you start calling me sir from now on," Jack advised.

Elsa once again had to hold herself back, this time from rolling her eyes. She had a feeling this one had a bit of an ego on him. "Oh, right. Sorry sir," Anna playfully bonking herself on the head. "So, what would you like us to get started on? Need something typed? Proofreading an email?" she asked. Anna had been genuinely excited about starting a real job. She didn't have any plans on climbing up the business ladder like her sister, but she just wanted a _real_ life experience. To see what it was like to have to get her hands dirty for once.

Jack chuckled. "Eager to get started. I like that. For now we'll keep it simple though. Anna, I'd like you to stay here and organize some of my files for me," he said gesturing to one of the large file cabinets over to the side of the room. "Elsa, I have one of the other girls waiting outside. Tell her to bring you along to get the coffee this morning."

Anna smiled and gave a salute towards him. "Aye aye sir!" she said before making her way off towards the cabinet.

Elsa on the other hand didn't look pleased. "A coffee run?" she asked crossing her arms.

Jack smiled. "Sorry, is that a problem?" he asked.

The two locked eyes for a few moments. "Of course no _sir_," she said before turning around and making her way out. Jack watched her as she left, admiring how her hips swayed back and forth. He then turned towards Anna, who was bent over and taking a look through the first drawer.

The pretty little thing looked confused. This was likely the first time she had ever actually seen a file cabinet. "Need any help?" Jack asked amused.

"Uh... no sir, I think I can figure this out!" Anna said giving him a thumbs up. Though it was clear she was very nervous. She didn't want to seem like she was clueless on the first day. She was sure alphabetizing these would be simple once she got started. She just needed a little time to sort it out was all. 

* * *

Elsa had been more than a little peeved as being put on coffee duty. Not that she hadn't expected to be given busy work, but did he really think her skill set was so small this was all she was capable of? Even organizing the files along with her sister would have been preferable. No, he likely only did it to annoy her.

She'd met up with the secretary outside, a women named Leiko who apparently went by Gogo. She wondered if all the women in the office had nicknames like that. She was a women with short black hair, and wore a yellow blouse and black pencil skirt. Elsa couldn't help but notice she had a rather... generous, backside.

Anyway, she told hrt that they'd had to walk to their regular coffee shop, which was three blocks down. Apparently driving was ill advised since their spot would almost certainly be gone by the time they got back, and they'd waste time having to circle around until another one opened. This was something she was clearly used to, because even in high heels Gogo was booking it down the street.

"Could you slow down a bit?" Elsa asked annoyed. She was struggling to keep up.

"I can't actually. God, why did they have to stick me with the new girl..." Gogo muttered.

Elsa frowned. "I'm not exactly happy about this either you know. And why are you in such a rush. The coffee shop isn't going anywhere..."

"I'm in a rush because we're being timed, and if I get caught up in the morning rush and end up late, I'm in trouble. Not everyone's dad can keep them from getting their butt whacked around here," she said bitterly.

Elsa looked surprised. "Does he seriously punish you for being late with coffee?" That was just plain petty.

"He punishes us for every little thing he can get away with punishing us for. Now can you please pick up the pace? I don't feel like having to stand at my desk today," Gogo said. Elsa did her best to keep up with the other women. She certainly hadn't wanted to slow her down and get her in trouble. As they walked through the street, quite a few people, mostly men, cat called and wolf whistled at them. Elsa shot them a glare, but Gogo waved it off. "Ignore them. You'll get used to it."

"You shouldn't have to get used to it," Elsa said irritated. "The way this entire office is run is absolutely ridiculous. When I take over all of this is coming to an end."

Gogo hummed. The very idea of Mr. Arendelle letting a women takeover his company, even his own daughter, sounded like a pipe dream to her. "Well, good luck with that. For now though we need to just bear with it." They eventually made it to the shop, and while it was a bit crowded they had beat the worst of the morning rush. They should have still had a bit of time to make it back. "Bit of advice. Memorize everyone's orders. If you get someone's wrong, somebody is getting a sore ass. They'll probably have you going with me the first few times, but I'll make you a list. Memorize it before they start you off in your own."

Elsa blinked. "My own? Do they really expect me to carry so much coffee back on my own?"

"It's not that much. We're only getting coffee for the guys," she explained.

"What?!" Elsa said annoyed. "You can't be serious."

Gogo clicked her tongue. "Deadly. You think the company is going to waste extra money on us? We get the instant stuff in our lounge room. Sometimes I get something for myself and a few of the girls here, but it's always on a separate bill. You buy your stuff with the company card and that's a surefire way for a whacked bottom," she explained.

Elsa fumed. This place really was like living in the thirties or something. 

* * *

Anna felt more and more nervous as time passed. She had absolutely no idea what she was doing. It wouldn't have been so nerve wrecking if Jack wasn't sitting right there at his desk. He didn't seem to be pay attention to her, but she couldn't help but feel her was thinking she was taking to long. Being inefficient or something.

Maybe she should try goggling it on her phone or something. No, she couldn't go browsing through her phone while the boss was here. It would be unprofessional. Maybe she should just try asking him. No, that would make her look like an idiot. Not that already didn't look like one now.

The door to the office suddenly opened and a girl made her way inside. Anna quickly recognized her as the girl from yesterday. The one they saw bringing her father and Jack coffee before scurrying out of the office. Anna had heard him calling for someone earlier over the intercom. She thought she heard the name Rapunzel. Jack looked up from his computer and smiled. "Ah, Punzie, good. I assume you know why you're here?"

Anna noticed just how nervous the girl looked. "To pick up where we left off on my correction sir..." she muttered.

"Exactly," he said getting up. Anna quickly turned back around, not wanting to seem like she was getting distracted. But she couldn't help but be curious about what was going on right now. She said she was being corrected. Did that mean she was being punished? Was she going to have to step out? At least then she might have a little time to figure out this file cabinet thing. "Fetch me the cane please."

She heard the girl let out a small gasp. Anna on the other hand was confused. A cane? Did... did he have trouble walking or something? She hadn't noticed anything like that before. She watched from the corner of her eye as the blonde slowly and reluctantly walked over to a large wooden cabinet on the opposite side of the room. Then she opened it up.

Anna had to bite back her own gasp at what was insides. Wooden paddles of varying sizes, leather straps, and what looked like a long wooden stick. The last one was what she ended up grabbing and bringing back to Jack. She held it out towards him, and he took it from her before swinging it through the air. Anna noted how the girl jumped at the swishing sound it made. "Now, bend over," he ordered.

The girl looked down before making her way over to his desk. She slowly bend over, laying her upper body across the desk, and leaving her rear pushed up and out. Jack swished the cane through the air a few times, and Rapunzel winced with each swing. Anna felt like something was caught in her throat. Was he... was he really going to hit her with that thing? She had never been spanked before, but she could only imagine how much getting hit on the butt with something like that would sting.

"U-um, sir..." she had finally managed to squeak out. Jack turned towards the girl who was blushing furiously. "Would you like me to step out for a bit while you...?" She couldn't bring herself to actually say what was about to happen right now.

He smiled. "No, it's fine. Just keep on working. I should be done with this one in a bit," he said tapping Rapunzel's bottom with the cane. She saw the blonde flinch and let out a small whimper.

Anna just nodded and slowly turned back towards the cabinet. How she was supposed to work knowing the women behind her was about to get her bottom whacked. She let out a small sigh and tried to focus on what she was doing. Someone's else's punishment wasn't really any of her business anyway.

THWACK!

"AH!"

Anna jumped and nearly dropped the folder she'd been holding when she heard the crack of the cane land down, followed by Rapunzel's yelp. She looked over her shoulder and saw the blonde wincing in pain, her hands gripping the edge of the desk, and one of her legs had shot up, like she wanted to kick out but had just barely stopped herself.

Before the girl could gather herself, Jack brought the cane back and swung again. It landed with another thundering THWACK, and followed by a cry from Rapunzel. Anna had turned her head around without realizing, now completely focused on the unfolding punishment. She watched as the cane had cut into her skirted bottom once more, and Rapunzel once again howled in pain.

Anna felt her blood run cold. That looked like it hurt, badly.

THWACK!

THWACK!

THWACK!

"Ouch! Ow! Oh! Oh! OW!"

She kept watching, unable to look away as Jack continued to slash into her cheeks with the cane. She let out yelp after yelp as she kicked her long slender legs out. After a bit, he finally seemed to stop. "Alright, lets get those skirt and panties out of the way."

This time Anna couldn't hold back her gasp. Luckily it was covered up by Rapunzel's. Had she heard him correctly? Did he really just order her to... bare herself in front of him? "Oh sir, no please. I've learned my lesson," Rapunzel whined.

Jack waved his finger. "Now, now, no whining. What will the new girl think seeing you act like that," he said smirking towards Anna. She blushed and quickly turned back around, earning a chuckle from Jack.

Anna felt totally embarrassed at having been caught, but still couldn't keep herself from peeking back over her shoulder. Rapunzel squirmed a bit as Jack pulled up her tight pencil skirt up around her waist, revealing a pair of pink frilly panties. Those didn't stay up for long however, as Jack grabbed them by the waste band and slowly pulled them until they were down around her ankles.

She couldn't believe it. He had really done it.

She could already see a number of pink lines marking the now bare cheeks. And Jack clearly intended to add even more. Anna was sure that while her skirt and panties probably didn't offer much, the sting of the cane would hurt even more on bare skin.

THWACK!

"OOOOOWWWW!"

Anna winced. That one had been aimed a little lower than the others, and seemed to hit a sore spot or something. Because it really got her howling. She kicked her legs out wildly, heels clicking against the floor. "Oh! Ah, that stings sir! Oh god!"

"Hold still Punzie," Jack said putting his hand on the small of her back to make sure she didn't try to get up. He tapped her bottom with the cane to get her to settle down, but when it was clear she wasn't going to stop squirming, he simply pulled back and swung again.

THWACK!

"OOOOOHHHHH!"

THWACK!

"AAAAAAHHHH!"

THWACK!

"OOOHHH! I'm sorry sir! I'm sorry!"

THWACK!

Somehow, it seemed like the strokes were landing even harder than before. Anna watched as line after line was added to the girl's bottom. She kicked and hollered, but never tried to reach back and cover herself. And for all her squirming Jack managed to keep her mostly in place.

Anna noted the ones that were aimed lower seemed to hurt the worst, and got the loudest yells from her. She wasn't sure just how long it had went on, but when it finally came to an end the blonde was left trembling and sniffling over the desk, her rear marked with crimson red lines of fire across them.

"You may stand," Jack said. Rapunzel stayed in place for a few more moments, until Jack gave her a slap on the butt. She gasped and then quickly scrambled up to her feet. "You can put your panties and skirt back now."

Rapunzel, not wanting another slap on the rear, quickly obeyed. She pulled her panties back up, and then rolled her skirt down, both actions causing her to wince when they went over her sore cheeks. "Can I assume we won't have anymore typos anytime soon?" Jack asked.

She shook her head. "No sir..."

"Good. You can go now." He gave her yet another slap on the rear as she scurried out. Anna watched her, an almost hypnotized look on her face. "Was that the first time you've seen someone caned?" Anna whipped her head around back towards Jack, who looked more than a little amused at her expression.

She stood there silent for a bit before nodding. "Y-yes..." she answered.

"A little intense I guess. But Rapunzel's made quite a few mistakes in the past month, so she earned something a little harsher than usual," he said as he walked towards her. Anna flinched as he walked in front of her. "Have you ever been spanked before Anna?"

She gulped as she looked up at him. "Uh... no..."

Jack chuckled. "Well, I guess that was especially surprising for you then. But I wouldn't worry too much about it. Only a lot of mistakes or slow work earns that type of punishment. So it doesn't happen often. Maybe once or twice a month," he said. Anna bit her lip as she thought of how long it was taking her with this file cabinet. If that girl got spanked for a typo, she was sure taking as long as she had with filing to earn her a punishment. "Why don't you take a little break Anna. You've been working on that file cabinet for a while now."

Anna felt like her legs were made of jelly. He really had noticed. How couldn't he have? "A-are you sure. I mean, I can keep going."

"No, it's fine. Take a breather. It's not going anywhere after all," he said before turning back to his desk.

She nodded and began making her way out. He didn't seem like he was upset about it, but she couldn't help but feel this was going to come back to bite her in the butt. Both figuratively, and literally...


	3. Chapter 3

**A/N: Yes, I know its been a while. Yes, I'm still planning on updating my other stories. No, I don't have a set time frame for any updates. With that out of the way, I hope you enjoy this chapter!**

* * *

Elsa wasn't used to screwing up. Usually any task she was put on was completed promptly and perfectly. So needless to say, she felt more than a little ashamed when something as simple as buying coffee had given her trouble. With how tight a time limit they were on and Gogo's literal ass on the line, they were doing their best to make it back as quickly as possible.

Unfortunately in their mad scramble to make it back to the office, Elsa ended up tripping and spilling the half she had been carrying. To say she was embarrassed would have been the understatement of the century. They'd had to go back and reorder all of the coffee since Gogo insisted the other half would get cold and she'd get extra swats for it. And of course any chance they'd had on making it back on time was shattered.

To add insult to injury, a few passerby's and even people in the shop had made quite a few snide comments and gestures on what they were sure would be a well deserved spanking. How they even knew about it was beyond her, but it was more than enough to have Elsa blushing despite the fact that she was sure she'd avoid such a fate. And even then, knowing she wouldn't be punished didn't ease the guilt towards Gogo.

She'd told her it was fine and not to worry about it, though it was clear she was annoyed and dreading her punishment. When they got back all the guys in the office were smirking and making smacking noises with their mouths and hands. Elsa sent a few glares their way but it did nothing to really stop it. Gogo just took it in silence.

After they finished passing all the coffee out, Gogo said she was heading to her supervisor's office to face the music. Elsa insisted on coming along, hoping she could help the girl get out of this somehow. When they'd arrived she had been… surprised, to see just who was waiting for them.

"Late with the coffee huh Gogo? It's been a while since that happened. Looks like you're in need of a little reminder of how to be one time."

Elsa looked confused as she stared down at the young man. He was clearly younger than them both. He looked… like a kid. He couldn't be any older than eighteen or nineteen at most. How could someone so young be in a supervisor's position?

"Yes sir," Gogo said, the bitterness of the situation very apparent in her tone. "Should I fetch the cane for you?"

He hummed. "The paddle. We've got a lot of backside to cover after all," he said with a chuckle. Both Elsa and Gogo frowned at the joke, though the ladder turned and walked out to go get the implement for her punishment.

The young man watched as she walked off, a smile still on his face. He then turned towards Elsa. "Ah, you must be Elsa," he said. "Jack told us the boss's daughter would be starting here today. It's nice to meet you. I'm Hiro. Hiro Hamada."

Elsa held back a scowl, keeping an even expression. "A pleasure," she said. Was this seriously who was going to carry out Gogo's punishment? That fact that she was being punished at all was humiliating enough, but this just added insult to injury.

"The pleasure is all mine," he said nodding back towards her.

Elsa turned her head back towards the door, and then towards him. "Mr. Hamada. I know I'm new here and it really isn't my place, but… are you really going to punish her over something so trivial?" she asked.

Hiro shrugged "Afraid so. Gogo knows she's responsible for bringing everyone coffee, and she knows what will happen if she's late," he said. "All the girls in the rotation know how things work, and we never let any of them slide."

Elsa narrowed her eyes. "Sir." It felt so weird calling someone who was so obviously younger than hert. "The truth is it wasn't even her fault. We were only late because I spilled the coffee I was holding. If anyone is going to be punished it should be me." She just couldn't say nothing when she knew this whole thing was her fault.

And as much as she hadn't wanted to play up the boss' daughter card on the first day, she knew he wouldn't really go through with punishing her. So if she could spare Gogo a paddling she was willing to.

Hiro sat back in his chair. "Well Elsa, that's really admirable of you. It's good you're willing to admit to your mistakes. But, Gogo is your senior. She's the one who's overall responsible for both you and the job here. She had a punishment coming, and it's going to be carried out. Besides, I'm not exactly… uh, I'm not really sure about the specific details of your status here yet."

Elsa opened her mouth to speak again, but he cut her off. "But if it makes you feel any better, I was already planning on adding your swats to hers. So that bit of guilt you feel a bit when you're watching her take your licks could technically be a sort of punishment," he reasoned.

She scoffed. "Sir, you can't be serious! That's not-!"

Gogo suddenly came back in, carrying a large wooden paddle in her hands. She walked past the platinum blonde and presented the implement out towards Hiro. "Here you are sir," she said, unable to hide the bitterness in her voice.

Hiro got up and moved around his desk before taking the paddle from her. "I think you already know what position to take," he said nodding towards the desk. Without another word, Gogo bent forward over the desk, her already tight skirt stretching further of her rather generous rear like a second skin.

Elsa watched as Hiro lifted the paddle, pressing it up against her rear. He rubbed it back and forth against her cheeks teasing. He was clearly enjoying himself. She could see the word 'Late' carved into the paddle, which she could only assume the men of the office had done on purpose. Did they have a paddle for every occasion?

She didn't have much time to think on it however, as Hiro brought the paddle back. He lined it up, and then swung. The paddle landed with a thundering SMACK, and Elsa winced as it echoed through the room. The paddle had covered her entire rear, flattening it for an instant before bouncing off.

To Gogo's credit, while she had flinched slightly, she didn't cry out or jump. Hiro waited a moment before bringing the paddle back again. Then with another solid swing, smacked the paddle against her rear once more. Elsa could see Gogo gripping the edge of the desk tightly. She bit her lip, feeling both guilty and frustrated at what she was seeing.

SMACK!

SMACK!

SMACK!

The swats came at a steady pace, with Hiro only taking a few seconds to rub the paddle against her bottom before pulling back for another swing.

Elsa just stood in watch, not even realizing that her hands had wandered back to her own bottom, which was clenched tightly. She had never been spanked before. Her father had never so much as slapped her wrist. So she could only imagine just how painful each swat was. The fact that Gogo still hadn't cried out or leapt up in pain spoke volumes to how tough the girl was.

After a few more swats, Hiro finally lowered the paddle. Gogo shifted uncomfortably over the desk, obviously still feeling the sting of the barrage of swats. Elsa felt relieved to see that it was finally over, but then he spoke. "Alright, that's enough of a warm up." The blonde's eyes widened. Warm up? That was a warm up? "Let's bare that butt."

Bare?! Was he serious?! Surely he didn't expect her to…!

Gogo sighed before she stood back up, reaching back and rolling her tight skirt up until it was around her waist. Then then reached down and began pulling her panties down around her knees. Elsa watched in shock as she bent back over the desk, her backside now completely bare for the paddle. She could make out the faint word 'late' across her cheeks left from the previous swats.

"That a girl," Hiro said, tapping her butt with the paddle. He brought it back and then swung again. The SMACK once again caused Elsa to wince, and this time Gogo let out a grunt of pain. Another swat soon followed, and it was clear the Gogo was feeling these far more than she was before.

SMACK!

"Uh!"

SMACK!

"Ugh!"

SMACK!

"Mm!"

Gogo grit her teeth, her legs and rear shaking as Hiro continued to paddle away. Elsa could only watch as the girl's pump backside was turned a darker and darker shade of red with each swing. Before long the word 'late' was no longer faint, but very clearly seen across both her cheeks.

But Hiro didn't seem keen on stopping anytime soon…

* * *

Anna was no longer nervous. No, now she was downright afraid. Ever since she had seen what happened to Rapunzel, she found herself shaking and clutching her bottom rather than focusing on the task at hand. Even during her lunch break all she had been able to think about was how Jack had torn into the poor blonde's rear.

The way he had snapped line after line across her cheeks. How he had so casually bared her bottom and made her present herself to him. She just couldn't get the image out of her head. Now she was back in his office, still struggling to figure out just how to organize these files.

Before she was only worried about looking incompetent. But now she was worried about her rear meeting the same fate as Rapunzel's. She'd already had a hard time focusing before, and not being able to get that thought out of her head was making things even worse.

"How are things coming along Anna?"

The girl gasped and looked over her shoulder to see Jack standing behind her. She hadn't even noticed he had gotten up from his desk. She shot up to her feet. "I… I'm not quite finished yet. I'm sorry sir," she said quickly, fiddling with her fingers.

Jack hummed, and then looked down towards the cabinet. "You look like you've been having a little trouble there Anna." She could feel her legs shaking as she looked back up towards her. "Anna, be honest with me. Have you ever filed anything before?"

For a moment she just stood there in silence. She felt like a little girl who'd been caught with her hand in the cookie jar. She knew if she told the truth she'd be admitting to wasting his time. But she couldn't just lie to him. Not only would it be obvious, but she'd only be digging herself into a deeper hole.

"N-no sir… I'm so sorry. I thought I could figure it out, but I just… I'm sorry..."

Jack nodded, as if he didn't already know. "I see. That makes sense." He had to admit, Anna looked quite cute all nervous and jittery like this. She was like Honey and Punzie before he properly broke them in. "That's disappointing."

Anna bit her lip as she looked down at her feet. She couldn't bring herself to look him in the eyes right now. "Are… are you going to spank me?" she managed to mutter out.

"Are you scared of being spanked?" Jack asked amused.

She nodded. "Yes sir…"

Jack chuckled, and Anna flinched as he reached a hand up. This was it. He was going to pull her to the desk, bend her over, and cane her. Her bottom was going to look like a red and white zebra skin. She then looked confused as he cupped her chin, tilting her head up to look at him.

"Don't worry Anna. I'm not going to spank you," he assured. "It's your first day, and at least you were trying your best."

Anna blushed, looking up at him surprised. She had been so sure a punishment was coming her way. "Really?" she asked.

He nodded. "I appreciate your pluck. But just make sure if you don't know something next time to just ask. I can show you everything you need to know."

She smiled up at him, a wave of relief flooding over her. "Thank you sir. I'm so sorry about before. I promise to learn everything as quickly as possible," she said.

"That a girl," he said, winking at her. She felt her cheeks heat up. He really was handsome. And pretty nice too. At least to her. Her first day didn't go as smoothly as she had liked, but maybe things would work out after all.

* * *

Elsa sighed as she made her way into the limo in front of the building. She knew today had been… horrible. After Gogo's thorough paddling, she'd been made to stand outside the office. Her rear serving as both a warning to the other secretaries, and eye candy to the men making their way by her. They'd chuckled and made snide little comments, and though Gogo told her she was used to it and she was fine, Elsa still felt annoyed.

But not as annoyed as she would be later. After Gogo, she had been made to shadow a few other secretaries, all who had menial and pointless jobs that had nothing to do with the actual business of the office. While they had managed to avoid the same punishment Gogo had suffered through, their bottoms did not go unscathed

All throughout their office they had their rears pinched, patted, and slapped. When Elsa angrily asked why they allowed this, they simply said it was how things worked. It sucked, but it wasn't worth making a fuss and risking punishment. No one had actually touched Elsa herself, but they did it so casually in front of her, the daughter of their very own boss, without any worry of repercussions.

This place really was terrible.

"Hey Elsa!" Anna said as she opened the door and made her way inside the limo. She slid next to her sister, a smile on her face. "How was your day?"

"Horrible," she answered. "Daddy really must want me to give this up if he expects me to spend a year here. I can't believe what goes on in this office. It's downright disgraceful. And the men here are just… uh!"

Anna hummed. "Sounds like you had it pretty rough huh? But hey, don't be too quick to judge. I actually had a pretty nice day. Jack showed me a whole bunch of stuff to help me get used to the routine around here," she said happily.

Elsa narrowed her eyes. She hadn't spent much time with him, she barely even knew him. But she just couldn't help but think he was a sleazeball. Anybody who let their office be run like this had to be. "I'm not sure you should be so trusting of him Anna. He might be up to something."

Her sister frowned. "But he's so nice. Yeah he punishes the girls and stuff, but only when they make mistakes. And he's really helpful and charming… I wonder if he's single."

Elsa shook her head. "Really Anna? Putting aside that that relationship would be totally unprofessional, I saw a woman be punished over coffee of all things today. This place is a madhouse."

"To us maybe. But we just got here. We don't know how everything works. For all we know those girls might have deserved to be punished." Jack had been so nice and patient with her, she just couldn't see him being so vindictive. Surely when he carried out punishment it was because he had a good reason to, right?

Elsa sighed. "You can be so naive Anna," she said causing her sister to pout at her. She figure Jack would show his true colors at some point, but when he did it wouldn't matter. She was going to win this little bet with her father no matter what.

And when she did she'd kick him and every other member of this glorified boy's club on to the curb.

Anna on the other hand sat back and smiled to herself. She was looking forward to spending more time with Jack. Maybe she would stick around here for good if things worked out.


	4. Chapter 4

"So, we finally get a crack at the boss's daughters tomorrow, right?"

Jack looked up from his phone and towards the young prodigy of the office, Hiro. He and a few of the other guys from the office were sitting around a table at one of their favorite local bars. They enjoyed meeting up to discuss matters after work and just enjoy some downtime.

Hiro himself wasn't even old enough to drink. But he was good company so the guys allowed him along anyway. They had sort of taken him under their wing.

The boy was new to the office, only starting a few weeks ago. And he had been enjoying all the perks that came with his position every chance he got. He'd been all too eager when Jack had told everyone that Anna and Elsa would be working there with them. He had spotted the sisters on the day Mr. Arendelle stopped by to introduce them, and ever since had been dying to get a shot at them.

The only reason he hadn't already is because of their 'Grace Period'. Otherwise Jack was sure he would have punished her right along with Gogo on her first day. "Elsa is free game. But leave Anna to me," he said before taking another sip of his beer.

Henry, or rather Hiccup as Jack and the others had affectionately nicknamed him over the years, hummed. "You've been keeping Anna awfully close to you Jack. Bit surprising. I figured Elsa was more your type." While he had always known Jack to go for the more bubbly sort of girls like Anna, he also knew he had a thing for the no nonsense types. Plus appearance wise Elsa had Jack's preferences to a tee.

Jack chuckled. "Oh, she is. But I have to be careful with Anna. Unlike Elsa she doesn't have a real reason to stay when things get heated, so I have to break her in without actually scaring her off. Throwing her to you guys would send her running for the hills."

A big paycheck and other bonuses are what kept the other girls around. And he knew Elsa didn't intend to go anywhere with that deal with her father in place. But Anna always had her father to run back to if she wanted. So Jack was being careful with the younger Arendelle sister. He wanted to have both of them around to play with after all.

"Always thinking five steps ahead, aren't you Jack?" Flynn asked, smirking. "Wish I was that good at breaking girls in. Cassandra is still giving me trouble. When are you going to be finished with Punzie?"

Jack waved him off. "I'll reassign her back to you tomorrow. But try not to get too wrapped up with her. You still have to deal with Cassandra after all." He figured he had hogged Rapunzel's pert rear for himself long enough. He'd be busy with Anna anyway.

HIro frowned. "You've got to be kidding me. You're complaining about not having two secretaries all to yourself while I don't even have one?" he asked before turning to Jack. "At least tell me that when you're done with Anna she can be assigned to me." He knew there was no way he was going to give up Elsa.

"Calm down Hiro. We'll get someone assigned to you soon. Maybe I can move some things around and have Gogo put under you. Honey Lemon too if things play out right."

The young prodigy smiled, very much enjoying the idea of having Gogo's big bottom at his mercy. And Honey Lemon would be a nice bonus as well. "Cool."

"Does that mean you're planning on taking both sisters then?" Hiccup asked, raising an eyebrow. "Playing things a little risky with the boss's daughter aren't you?"

Jack just shrugged. "If there's no risk, then what's the point?"

* * *

Both Anna and Elsa had very different views on how their first week at work went. Anna was very much enjoying herself. Jack took time to teach her everything about filing, basic computer skills, email and document formats. It was a bit much to take in, but he was very patient with her. They had a lot of nice chats, ate lunch together, and she just enjoyed being around him. The only semi awkward moments had been whenever he'd call in girls to punish, but Anna was slowly getting used to it.

Elsa on the other hand found herself growing more miserable by the day. Each day she'd been told to shadow one of the other secretaries, where she got a firsthand look at just how tough things were for them. If they weren't having their bottoms spanked for the most minor of offenses, they were being groped, pinched, or patted.

Again, nobody had made a move towards Elsa herself, but that didn't make her feel any better about having to sit and watch it all happen in front of her.

It also annoyed her that Anna seemed oblivious to the problems of this office. She knew that she didn't get to see as much with her always inside Jack's office, but she seemed completely oblivious to the vibe their co-workers were giving off. When she'd confronted the girl on it, Anna reasoned that they must be doing something wrong.

After all, Jack was nice. Surely he wouldn't allow such punishments to carry on under his watch unless they were warranted, would he?

Elsa had given up trying to convince the girl. If she wanted to turn a blind eye and keep defending him, then that was her decision.

"Morning Gogo," Elsa greeted as she made her way into the break room. "Ready to make the morning run?" Despite not having been at it so long, she had managed to more or less get the hang of their coffee routine. This has mostly been motivated by her not wanting to see the girl get paddled on her behalf again.

"Sorry, but you're going to be on your own this time," Gogo said. Elsa looked at her confused. "I'm being reassigned. Seems like they're finally giving that little runt Hiro his own secretary, and I drew the short stick."

Elsa winced. She couldn't imagine that would be a fun experience. Hiro, being the youngest of the men here, had always been the most eager and open about ogling and pawing at them. He seemed to have a particular liking for Gogo too, she noticed. "Sorry to hear that…"

"So am I. But you should be more worried about yourself. You going to be alright making the morning run on your own?" she asked.

Elsa nodded. "I should be fine." She could at the very least keep up with Gogo at this point, and the girl always managed to get back early, so she figured she would break even time wise. "And at the very least you won't be getting in trouble if I screw up."

For just a moment, an odd expression passed across Gogo's face. "Yeah…" she muttered. "Just make sure you hurry. You still don't want to be late."

"Of course not," Elsa said. She may have been pardoned from punishment, but she didn't want to give Jack an excuse to badmouth her to her father. "Be back soon. I'll try to grab you an extra coffee from the shop."

"Thanks…"

Gogo watched as she headed off, feeling a little bad. Elsa seemed like a pretty smart and determined girl. She felt bad about what was without a doubt going to be a rude wake up for her today. But she knew if she warned her about her grace period being over, it'd be her own bottom in the crosshairs.

Meanwhile, in Jack's office, Anna stood before Jack and gave him a salute. "Good morning sir! Reporting for duty!" she said excitedly.

Jack smiled back at her. "And good morning to you too Anna. You seem awfully energetic for a Monday. I like that," he said chuckling.

She shrugged. "Well, it's just another day after all." And the fact that it was another day she got to spend with him didn't hurt either.

"That's a nice attitude to have Anna," Jack said, patting her on the head. She beamed and blushed. A part of Anna felt that Jack was only showing her so much attention because he could tell how inexperienced she was. But she still liked having so much of his attention. "So Anna, do you think you're getting the hang over things around here?"

She nodded. "I think so sir. You've been doing a great job showing me everything. I mean I'm sure there's still some things I have to pick up, but the basic stuff I got down," she said confidently. She didn't have to spend half a day filing a single cabinet anymore, and she knew how to complete the basic task he would need computer wise.

"That's good," he said nodding. "Because I wanted to give you a little test just to see how much you've improved. Don't worry, it's nothing too crazy. Just some more filing."

Anna hummed. "Oh, okay. That sounds simple enough." She supposed it was only right that he made sure she really was learning and paying attention to what he showed her. Jack headed for the door, motioning for her to follow, and she quickly scurried after him.

He led her down the hall and then stopped in front of a room Anna hadn't seen before. Jack opened the door, and Anna's eyes widened as she saw a number of file cabinets inside. "Oh wow, that's… that's a lot of file cabinets…" she said.

"All I need you to do is sort through these. You can do that for me, can't you Anna?"

The girl looked around the room, but then nodded. "Y-yeah. I'm sure I can sir. Don't worry." It would certainly take some time, but if she just remembered everything he taught her there wouldn't be any problems.

"Good enthusiasm! But since this is a test you should know that I'm going to be timing you," he explained.

Anna looked at him confused. "Timing me?"

He nodded. "That's right. A good secretary has to do her work both correctly, and quickly. So this will give me a good measure of how fast you work."

"How long will I have?"

"Don't you worry about that Anna. I promise you'll have more than enough time. Just do the best you can and work at your normal pace," he said smiling as he cupped her chin.

She couldn't help but smile back up at him dreamily. "Okay…"

"Oh, and as some extra incentive, you should also know that if you happen to run out of time then you'll be getting punished."

Anna's eyes went wide once again. Had he just said… surely he didn't mean that, did he? "Um, sir. When you say punished, do you mean you're going to… uh?" She blushed and looked down, shifting nervously. She couldn't even bring herself to say the words. "Do you mean I'm going to get a… you know?"

"A spanking?" Jack said chuckling. "That is generally what punishment entails around here Anna. But don't worry, that's just if you can't finish in time. You said to yourself that you're confident you can do this, so it shouldn't even be an issue, should it?"

She could feel herself starting to panic. Somewhere in the past week she had just assumed that she was exempt or immuned to such punishments. He'd had plenty of reason to spank her last week, but hadn't taken a single chance. Now he was casually hanging it over her head, and it had totally caught her off guard.

Her thoughts were interrupted when he tilted her chin back up, and she blushed deeper as she found herself staring into his eyes. "Well Anna?" he asked.

She felt her legs start to get wobbly again. What was she supposed to say? She didn't want to agree to getting spanked, but she also didn't want to seem like she was trying to take the easy way out either. Every other secretary around here had to follow the same rules, and it would be childish to ask to be treated differently because of her father.

This was supposed to be her first real job, and she had to treat it like one. Even if it meant taking the small risk of having her bottom smacked…

"No sir, no problem at all…"

Jack nodded. "Good girl! I'll be in my office. Come see me when you've finished up," he said, patting her on the head one last time before turning around and heading out.

The moment he left, Anna felt her heart pounding. She had no idea how much time she had. No idea what shape each cabinet was in. But Jack had said she had more than enough time, didn't he? She just had to do her best. If she tried to rush she was sure she'd mess something up. Go at her regular pace, and she wouldn't have to worry about… that, happening to her.

Jack smiled as he made his way back down towards his office. The filing room was one of the many tricks that he'd been taught by Mr. Overland himself, so it was sort of ironic that he was using it to break his daughter in.

He knew she was probably panicking right now. Doing her best to not think about what would happen if she failed this little test. She might start panicking, rushing to get it done and screw something up, costing herself time. Or she might be able to keep herself collected throughout the whole thing. It didn't matter.

He had done this enough times to know that the fastest anyone could finish sorting through all those cabinets was an hour and some change, maybe just an hour even if they were rushing. But no matter how quick she got it done, there was no way she was going to do it within the time limit.

Because there was no time limit.

Was it underhanded? Sure. But as Mr. Overland had told him years ago, it does every girl good to get her bottom warmed starting out. She'd be better for it later. Besides, it was better that he eased her into her future routine himself than let the guys have at her. He wondered just how Elsa was faring.

* * *

Elsa hadn't made it back with the coffee as quickly as usual, but considering that she didn't have Gogo with her that was to be expected. She had still made pretty good time despite the fact that she was pretty sure the guy at the counter had been deliberately delaying her order.

When she got back she set the coffee down on the table in the lounge and began to sort through them. "Morning Elsa." She looked over her shoulder and then saw the smug face of one Flynn Rider. Or so he claimed. From what she heard from the other secretaries, his real name was far less flattering.

"Good morning sir," she said, turning her attention right back to her task. It was bad enough she had to call someone like him sir, but she wasn't going to give him anymore attention that he deserved. Which was none.

He chuckled. "Finished up with the morning coffee run huh? You made it back in pretty good time. Was a little worried that without Gogo you might have some trouble."

She hummed. "Well sir, as you can see even on my own I somehow managed to complete the daunting task of buying coffee for the office." Every word was dripping with sarcasm, but she just didn't care enough to try and place nice with him.

"That you did," Flynn said before reaching past her. "Here, let me make your job a bit easier and just grab mine." She frowned as he took his time grabbing his cup. She didn't like just how closely he was leaning over right now. "There we go. Thanks again Elsa."

"You're welcome sir…"

She wouldn't wait for him to take the thing and get out of her hair. At least it would be one less stop she'd have to make when she passed everything out. "Keep up the good work." Elsa waited for him to finally get lost, but then suddenly felt a sharp smack to her rear. She flinched, and her eyes widened.

For the moment she just stood there, shocked at the tingly feeling in her left cheek. Then she slowly turned her head and looked over her shoulder. Flynn smiled and winked at her before turning and walking out, and Elsa just kept staring.

Did he…? Had he really just…?

He'd slapped her bottom!

She glared angrily towards the door where he left. How dare he! What in the world had gotten into him?! Had he somehow forgotten just who she was? Or was he just pushing his luck and playing dumb?! Her first instinct was to rush after him and give him some rather choice words, but she didn't want to go making a scene.

No, blowing up and yelling at him would just end up making her look bad, and that was what Jack and her father wanted. She needed to approach this with a cool head. Still, something had to be done. She didn't want him or anyone else thinking this was okay. She was going to make her rounds with the coffee, then go talk to him.

She took a deep breath and then grabbed a few cups before making her way out. As angry as she was, she still had a job to do. The first person she stopped by was who she probably considered the most tolerable of the men in this place. Henry Haddock.

"Good morning sir. I have your coffee."

Henry, or Hiccup as she had heard some of the others call him, smiled. "Ah, thank you Elsa. I was starting to get a little worried there. You're a bit later than usual."

Elsa wouldn't say she was fond of anyone in this office, but Hiccup at the very least had the decency not to act like a horny little schoolboy. She rarely caught him eyeing her up. And even though Astrid and Merida complained about him, they were willing to admit he was probably the least demanding of the men.

"I'm sorry. This is my first time getting the coffee on my own. I'll try to be more timely in the future," she said. There was only so much faster she could be on her own. She just didn't think she'd ever be as fast as Gogo.

Hiccup nodded. "Well, just do your best. Thanks." He took the coffee from her, and as she turned to leave she suddenly felt him pinch her butt. Elsa gasped, nearly dropping the rest of the coffee. "Uh-oh, careful there. We wouldn't want you spilling that."

Elsa's cheeks turned red, and she looked back towards him in disbelief. Hiccup just smiled back towards her, as if he had no idea what she was gawking at him about. "You really should get going shouldn't you? You wouldn't want to end up being late handing those out. You could get into some real trouble," Hiccup advised.

Elsa stood for a few more moments. First Flynn, and now Hiccup. This… this was not a coincidence. She could write the former off as a fluke, but him? He had to know full well who she was, and he wasn't the type who seemed to like pushing his luck like this. Just what in the world was going on?

* * *

**A/N: Bit more setup than anything in this chapter. Some more spanks and other stuff will be coming in the next one.**


	5. Chapter 5

**A/N: So no actual spanking in this chapter, but I thought the build up to this whole thing was important and it was getting a bit long. So the next one will pretty much jump right into it. I'll try to have it out quickly. Hope you guys enjoyed. **

* * *

Elsa hadn't known what to say after Hiccup's little stunt. Well, she knew what she wanted to say, but again, she just would be playing into their hands. So she choked down the storm of insults she'd been prepared to fling at him and simply walked out, deciding to deal with him later along with Flynn.

But it was after that it became abundantly clear just what was going on. She'd gone by Hiro's office next. He'd smiled and taken his attention off of poor Gogo, who once again bent over his desk for a round with the paddle, and thanked her. She didn't even get the chance to turn all the way around before he'd given her a slap on the rear.

Once again, Elsa was floored by the blatant act of disrespect. This time however she walked out immediately, feeling like she would blow up if she stayed any longer. She took a few moments to cool herself down before moving on, but it wasn't long until she found herself riled up again.

Every single male she delivered coffee to rewarded her with a slap or pinch to her backside. Even when she tried to walk out backwards, they'd reach around just to get to her rear. By the time she had finished handing everything out, her cheeks had a warm tingly feeling in them.

She had gone to the bathroom afterwards to collect herself, and then thought carefully on how to approach this. Was this some sort of mistake? Had they all lost their minds? She just couldn't fathom what would embolden them to put their hands on their boss's daughter like this. Did they really think this was okay? Or did they all just meet up and decide to take one collective risk? Maybe they assumed they couldn't ALL be fired?

At the end of the day it didn't matter. All that mattered was that it needed to stop. So she went straight to the top. "What can I do for you Elsa?" Jack asked, sitting back in his chair and smirking. Elsa really couldn't stand that smug face of his. He really did think he was untouchable, and it irked her to no end.

"I'm sorry to disturb you sir. But I have an issue I wanted to address," she said, trying her best to keep her voice calm. Jack nodded, signaling for her to go on. "Some of the men in the office… have been acting strangely." And by some, she meant all.

"Really? How so?" he asked.

She got the feeling he knew damn well how, but she spoke anyway. "You see sir, some of them have been touching me in ways one might consider… inappropriate. A number of them have placed their hands on my… my seat." That was the least provocative word she could think of for the word butt, but she still ended up blushing somehow.

Jack hummed. "Is that right?" he asked. "Well, I can see why something like that might have caught you off guard and worried you. And I'm glad you felt comfortable enough to come and talk to me about this." As if she had any other choice. "But I don't really think it's anything you should be too worried about."

Elsa narrowed her eyes. "Excuse me?"

"You see we recognize how hard you ladies work around the office. And we've found a great way to express our gratitude is with a little pat or pinch to the rear. It's our way of adding a little emphasis to our thank yous, and keeping you girls moving so you can continue doing a great job."

Elsa looked annoyed. Was he serious right now? He wasn't really trying to sell that nonsense to her, was he? "Well sir, as much as I appreciate the thoughtful gesture, I can assure you that a simple thank you will suffice. So if you could please ask the others to refrain from touching me, that would be just splendid."

Jack shrugged. "I see. Well, if it really makes you so uncomfortable then feel free to let them know. I don't think anyone should have any problems respecting your decision."

The blonde hummed. Not touching her butt was something she really didn't think she should have to tell them. "I'll be sure to do that sir."

She turned and got ready to leave, but then Jack spoke. "Oh, Elsa. Around here secretaries must ask to be dismissed before leaving," he informed.

She scoffed, but turned back around. "My I be dismissed, sir?"

"You may."

She quickly turned around and made her way out. She knew the whole reason her father was making her do this stupid trial was to test her patience, and as much as she hated to admit it, it was working far too well.

Jack watched her as she headed out. It had been the right call to let the guys handle her for now. She carried herself with a lot of pride, and having them put her in her place rather than him would be a much bigger blow to it. He knew it wouldn't be long until he spoke to her again. But for now cute little Anna was getting all his attention.

And speaking of Anna, it was about time she wrapped up with her little test…

Meanwhile, Elsa fumed as she made her way towards the breakroom. This office, this company, it was all so insanely stupid. The minute she worked her way up she was reworking this entire system of things. Or maybe she would just flip them. See how the men liked a taste of their own thought of doling out revenge on Jack for all the women off the office was quite a tempting one indeed.

Her thoughts of vengeance were cut short however when she saw Gogo in the breakroom, scowling and rubbing what was obviously a very sore backside. "Are you alright?" Elsa asked. Gogo looked over and gave her a look that questioned just why she'd ask such a silly question. "Of course not. Sorry."

Gogo sighed. "It's fine. Just… been a while since I've been worked over like this," she explained. "Little brat is pegging everything he can on me. I'm not sure I'm gonna make it through the week at this rate."

Elsa frowned. Here she was fuming about a few pats and pinches when the others were getting far worse. She made a mental note to recruit Gogo to her office and give her a big raise once this test was over. "Gogo, can I ask you something?"

"Sure. Not like I'm busy right now."

"The policy in the workplace is that female employees can be disciplined by the men. That part I understand. It's not optional. But… are they allowed to touch you when discipline isn't involved? If not, why do you let them?" she asked. She just couldn't understand why Gogo and the others would allow the guys to swat and pinch at their bottoms all day. It didn't make any sense.

Gogo sighed. "So you talked to Jack about it huh?" she asked. Elsa nodded. "Alright, here's the thing. They're technically not allowed to touch us outside of discipline. So if we ask them to stop, they have to. But if you do… well, they make things a lot more crappy for you around the office."

Elsa raised an eyebrow. "How so?"

"They add onto your workload. Way more than anyone could handle in a day. Then they each nail you for something," she explained. "My second week here they did the same thing. When I asked them to stop, I got a truck load of work assignments. Never even got close to finishing them. Burned out all my write ups, and I was pretty much running from office to office just to get my butt whacked for it."

Elsa scoffed. "You're kidding? They shouldn't be allowed to do that."

"Sorry to say your dad doesn't feel the same way. Eventually I did what everyone else did, caved and played along. It's just easier that way." Nobody wanted to spend every day of the week getting swats from every guy in the office. "Sorry about not warning you about your grace period being over."

"My grace period?" she asked. She never heard anything about that. Was that what all of this sudden boldness from the men came from?

"It's what they do for all the new girls. They give them a pass for the first week. Act all nice and polite. Make you think you're the exception or special. Then they catch you off guard the next week and put you through the ringer."

The blonde looked irritated. "You're kidding me?" Just how much thought did these people put into harassing the girls around here?

"Sorry, no. I would have told you about it earlier, but anyone who lets it slip ends up getting a target on their butt too. And I really can't afford anymore personal attention on my ass right now."

Elsa sighed. "No, it's fine. I understand." There was no reason for her to keep risking her own butt on her account. "I just find it hard to believe the past week was supposed to be them buttering me up." Making her feel special? Hardly. All they made her feel was annoyed and frustrated. But…

...Anna on the other hand…

"Shit!" she muttered. This explained why Jack seemed to be keeping her so close and treating her so nicely. He'd been setting her up for today. Gogo looked confused as Elsa began making her way out.

Just as she was about to head through the door though, she was cut off by Fynn. "Hello there Elsa," he said smirking down at her. "I was wondering if we could have a word."

* * *

Anna stood nervously as she watched Jack skim through the file cabinet. She had gone through them as quickly as she could without rushing. She hadn't really paid attention to the time. She thought it would just throw her off. She just wanted to focus on getting the task done. It seemed like the right call, but a tiny part of her was wondering if she should have taken a bit more time.

The walk to the office had been nerve wracking, and even now she had a sinking feeling in her stomach. She wanted to ask how everything was, but she was too afraid to.

Eventually Jack stood up and turned towards her. She tried to look calm, but Jack could see the nervousness on her face. "Well Anna, I'm happy to say that your organization skills are excellent. Everything is exactly where it should be," he said.

Anna felt a bit of relief at hearing that. "Thank you sir," she said nodding.

"Yes, everything is absolutely perfect. I'm proud of you," he said patting her head. She smiled, this time more genuinely, and felt her cheeks heat up. Maybe it was childish to feel so happy at his praise, but he couldn't help it. "Unfortunately, you just barely went over the time limit. By just two minutes."

Anna's eyes widened, and she felt her heart stop for a moment.

Two minutes.

Just two little minutes.

She panted, feeling her legs begin to get wobbly. "So, Anna you do know what that means don't you?" he asked. The girl looked like she was in a daze. But after a while, she nodded. "What does it mean Anna?" he asked.

It took her a few moments to get the words out, and even then it was in a low mutter. "It means you're gonna spank me…" she whispered.

Jack nodded. "That's right. Sorry Anna. I know it's silly. It was only two minutes, but rules are rules," he said cupping her chin. "You understand, don't you?"

She was forced to look him in the eyes as he raised her chin. "Yes sir, I understand…"

"Don't be too nervous Anna. I won't be too hard on you. I'm still very proud, and it was only two minutes. A nice warm up spanking should be enough."

Anna was sure that a warm up spanking was technically him taking it easy on her. She had seen the differences in spankings for different offenses. But for someone who had never been spanked in her life, the idea of it happening at all was still terrifying.

The idea of him having her over his lap or his desk, his hand making contact with her bottom. Was it going to be over her skirt? Her underwear? The bare? Either way it was going to be so intimate. More intimate than she had ever been with any man before. Her hands slowly made their way to her bottom as she got lost in her thoughts.

Jack smiled at her reaction. "How about we save your punishment until after lunch. For now we can just head back to my office," he said before nodding towards the door.

She flinched. "Oh, yes sir…"

Jack nudged her towards the door, and Anna made her way out and headed towards his office. Two minutes. She had been so close! Just two minutes! She glanced at the clock on the wall as she walked. In a few hours, she was going to get the first spanking in her life…

* * *

"That's ridiculous!"

"I'm sorry, but it's true."

Elsa glared at Flynn, who stood with a smug look on his face. When he had told them they needed to have a word, Elsa imagined he had some stupid errand to pass on her. She hadn't been expecting to be accused of messing up. An accusation she was one hundred percent sure wasn't true.

For as much as she hated having to make the coffee run, she had been sure to write down each and every order correctly. So the idea that she had brought him the wrong one somehow was unbelievable. "Sir, I know that I brought back the correct order. I wrote it down this morning just as you said. It's the same order you've been getting for the past week," she said sternly.

Flynn shrugged. "I can see how you might have been thrown off, but I ordered a cappuccino today. Not a frappe. Wanted to change it up," he said. "It's an easy mistake to make, but a mistake nonetheless."

Elsa glared at him. He was lying through his teeth, and he wasn't even trying to be clever about it either. "Sir, are you sure you weren't the one who made the mistake here? I've been very thorough when it comes to memorizing and writing down orders," she said crossing her arms.

He chuckled. "I'm sure you have. But everyone slips up every now and then. Today just happened to be your day," he said simply. "Now as for the matter of your discipline."

"My discipline?" Elsa asked in disbelief. He couldn't be…

"This is your first offense, so I wouldn't come down on you too hard. But I do think it's important to set a standard, you know?" he asked.

"You… you want to spank me?" she asked.

"That is generally how we deal with slip ups like this," Flynn said amused."Of course if you want to use one of your passes, you're free to. Just swing by the common area around lunch and let me know which you'd prefer. We can take care of it then."

Before Elsa could argue, Flynn gave her a pat on the butt and then headed out. Elsa looked on in utter shock. He just… he just told her that he was planning on spanking her! And so casually to boot! "That pig!" she said, bawling her fist up.

Gogo, who had just stood by and watched silently, decided to speak up. "Elsa, calm down. They're testing you," she warned.

"Oh, I know exactly what they're doing. But if he thinks I'm about to fold under pressure and let him have his way then he has another thing-!"

"I think you should let him spank you."

Elsa turned towards Gogo surprised. "What?"

"Just let him spank you Elsa. I know it sucks, but trust me, this is the best move you could make. Take the punishment and get it over with."

Elsa scoffed. "You have to be kidding me! I haven't done anything wrong! He's lying and we both know it! Why should I give in to him?!" she asked.

"Because if you don't, you'll be in even bigger trouble," Gogo said. "I know what you're thinking. You use a pass now, and just don't slip up again right? It's what all of us tried to do before. It doesn't work. It's too easy for them to pin things on us. They'll make you burn through them, and then you'll get an even worse punishment."

"So I'm just supposed to roll over and give up then? Play into their stupid little game?"

Gogo sighed. "Look, I'm just giving you my advice, okay? You can go at this kicking and screaming if you want, but it's gonna literally be a pain in the ass," she said as she made her way out. "You can deal with a little embarrassment now, or you can get your butt majorly fried later. Your call."

Elsa watched as she left, feeling more and more irritated by the second. Get spanked now or get spanked later? What kind of choice was that?

A part of her wanted to call her father. Ask just what the hell his employees were thinking. But… she had a feeling he already knew. If she called him, he wouldn't be the least bit surprised. She could already hear him asking her if she was ready to quit their little bet, and it infuriated her.

Besides, even trying to use him as a get out of jail free card would have felt like a loss in itself. It would make her little more than a daddy's girl in their eyes. She bit down on her thumb. Damn it, she felt like she was going to lose either way.


End file.
